Nothing about Alberto Toledo is loud. Not his clothes; not his voice; not his demeanor. It is easy to underestimate Alberto Toledo when you meet him at first. He is, for the lack of a less overused word, just a very humble person.

Humble as his origins, perhaps, when he sat on the porch of an unsteady house in São Paulo as a kid, sewing soccer balls in order to feed the family. But even at a young age he already had the determined look in his eyes that he still has today. Able to grasp an opportunity when it presented itself and driven by curiosity, he turned his first employment in an electronics shop that consisted largely of unscrewing TV sets and dusting off their interior into a springboard for an international career. He learned how to repair radios and TVs during the day while attending evening classes at school. “One day I’ll be able to fix even computers”, young Alberto declared. His colleagues laughed and called him a dreamer.

“One day I’ll be able to fix even computers”, young Alberto declared.

He didn’t just dream, he dreamt big. Alberto got an electronics degree from Divino Salvador College in São Paulo and actually did learn how to repair computers, more precisely, IBM System/360 mainframes that were used in Brazil’s big corporations at the time. Then he set eyes on a destination many of his friends hadn’t even heard of: Silicon Valley.

In 1984, he boarded a plane to the US with a student visa in hand. Having sold his few possessions gave him enough cash to live for a month. He either had to find a job quickly or return, defeated. Alberto still cherishes the unused return ticket as a memento. At a time when IBM was very successful, he started to work at a reseller. His boss at IBM ridiculed the new line of Personal Computers when it was launched what he called “Mickey Mouse computers”. But Alberto, who learned to program in assembly language, was fascinated by these new personal computers and dreamt of building his own. In the meantime, he had found love and later married this woman who hailed from Switzerland. When she became pregnant, the couple moved to Switzerland.

Alberto didn’t speak a word of German and he wasn’t made for the harsh winter weather, he recalls. But he still managed to land a job at Nixdorf which was producing IBM clones by showing the managers things they didn’t know. After two years as technical director at AST Research in Switzerland, he got promoted to a manager at the EMEA level and moved with his family to Limerick, Ireland, before moving to the company headquarters in sunnier climes of California again. This company was soon sold to Samsung, and it became Alberto’s responsibility to fire people, a task which he profoundly disliked.

“My grandfather always told me that opportunity is like a hair on a bald man’s head”, Alberto says.

Looking for a new opportunity he came across a young software company called Citrix Systems. The company couldn’t afford to pay him the same salary but would award him stock options instead. “My grandfather always told me that opportunity is like a hair on a bald man’s head”, Alberto says. And he grabbed it, by accepting Citrix’s offer in 1998. The stock price went up and up, except when the dotcom bubble crashed and it went down. That Alberto stubbornly held on to his stock, even after the price crashed from 120 to 5 Dollars, he attributes to his prudent mentality. “I didn’t panic because I’m no speculator, I’m just a steward of the wealth I was able to accumulate”, he says.

It took more than a decade, but the price of the stock recovered to the same level again. But working at Citrix was about more than money, it provided him with another opportunity. The company didn’t have a support presence in the EU yet, so Alberto eventually became Managing Director, service operations responsible for EMEA, based in Schaffhausen, Switzerland. This was a big personal sacrifice, Alberto recalls because his family was still living in the US.

His boss, who was VP Sales and Services, asked Alberto one day: “Did you ever think of doing sales?” “No, I’m an engineer, I can’t sell”, he replied. But his boss insisted and said he’ll do well, until eventually, Alberto agreed, under the condition that he could try his skills in a small territory first. This brought him to South America. In a few months, he closed a deal with a large Bank in Puerto Rico, the largest deal for Citrix in that region until then. Sales grew fast under Alberto, faster than in other regions, and the reason for that was that Alberto implemented the sales funnel approach that is widely used today. As an engineer, he naturally took comfort in numbers and urged his team to quantify in weekly meetings to commit to a forecast number and qualify their leads (today this is known as MQL and SQL approach). This method induced a positive competition among his team and inspired a work ethic to go after clients and think about all the different ways to approach them. In short, it took a Brazilian engineer to turn sales from art to a science.

In 2006, he left the corporate world at age 43, having accumulated enough wealth to live independently. “I didn’t do anything for 3 years. I went to the beach, I went cycling. It was liberating to have no more meetings”. But soon enough he realized that this way of life wasn’t fulfilling enough. “It always felt awkward to say “I manage my investments” when somebody asked me what I do”, he says. Work creates your identity and structures your day, and Alberto grew up with a strong work ethic belonging to the working class.

He wanted to get involved in something that was bigger than himself again, he explains. The stock market crash in 2009 was what triggered him to move, and he became involved in several companies since then: Autonomy, which was soon acquired by HP, and Mobiwork. As if this wasn’t enough for a change, he spent his weekend’s programming algorithms that try to identify trends in the financial markets, which informs his investment decisions.

“The greatest force that makes all people equal is that nobody knows precisely the future”, Alberto says. You can use as many variables and as much processing power as you want, but in the end, you’ll still only come up with a prediction. His investment philosophy is conservative; “I think it is my responsibility not to be foolhardy”, he says and adds that he’d never thought of squandering a big bonus when he received one. He sees it as a responsibility of people that come into wealth to educate themselves about financial instruments, embrace the idea of diversification, not to gamble or get greedy and balance very risky investments like startups with solid ones like real estate. But the best investment you can ever make is education, Alberto says. He used to work during the day and study at night. Later he did an MBA at the City University of Seattle. “My education has paid off multiple times and I always told my kids that they should get a good education”, he says.

Today, Alberto is Chief Strategy Officer of Beekeeper, a software-as-a-service startup that counts investiere among its investors. “My job is to ask the right questions”, he says. While his position doesn’t directly contribute to the bottom line of the company, he says that he is busy helping to create the kind of safe working environment that makes people put all their effort into contributing to the success of Beekeeper. For fast-growing companies like Beekeeper, it is a boon to have someone like Alberto who already has done this growth exercise before.

Alberto chose to work for Beekeeper because he wanted to work somewhere where he can add value in a business that he understands well. He’s also driven by a motivation to give something back. “I wouldn’t have achieved success if it were not for the kind help of many mentors that advised and coached me throughout my career. They saw something in me that I didn’t see in myself at the time and they were very patient with me. I feel thankful for that and I feel that now it’s my turn to fulfill that role for the younger generation”, he explains.

When he met Chris Grossmann from Beekeeper and his team almost 4 years ago, he was rapidly convinced that they have the necessary grit to succeed. As is often the case, he got to know them via an introduction from his personal network. “You should ask yourself what you would do if you didn’t have to work any longer. If your answer is that you’d still do what you do, you’re in the right place. That’s why I work for Beekeeper.”